Iodomethane oxidation by dimethyldioxirane:: A new route to hypoiodous acid and iodohydrines

被引:29
作者
Asensio, G [1 ]
Andreu, C [1 ]
Boix-Bernardini, C [1 ]
Mello, R [1 ]
González-Nuñez, ME [1 ]
机构
[1] Univ Valencia, Dept Quim Organ, Fac Farm, E-46100 Burjassot, Valencia, Spain
关键词
D O I
10.1021/ol9903281
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The oxidation of iodomethane with dimethyldioxirane allows the generation of stable neutral solutions of hypoiodous acid in the absence of any trapping agent for iodide anion. Hypoiodous acid is trapped in situ by addition to representative olefins to give iodohydrines in good yields. The stereochemical study of the products shows the anti-stereospecific nature of the iodohydroxylation reaction.
引用
收藏
页码:2125 / 2128
页数:4
相关论文
共 41 条
[1]   SYNTHESIS OF ANTHRACYCLINE C-GLYCOSYL ISOSTERES [J].
ACTON, EM ;
RYAN, KJ ;
TRACY, M ;
ARORA, SK .
TETRAHEDRON LETTERS, 1986, 27 (36) :4245-4248
[2]   A FACILE ROUTE TO IODOHYDRINS AND EPOXIDES BY OXIDATION OF OLEFIN-IODINE COMPLEXES WITH PYRIDINIUM DICHROMATE [J].
ANTONIOLETTI, R ;
DAURIA, M ;
DEMICO, A ;
PIANCATELLI, G ;
SCETTRI, A .
TETRAHEDRON, 1983, 39 (10) :1765-1768
[3]   EPOXIDATION OF PRIMARY AND SECONDARY ALKENYLAMMONIUM SALTS WITH DIMETHYLDIOXIRANE, METHYL(TRIFLUOROMETHYL) DIOXIRANE, AND M-CHLOROPERBENZOIC ACID - A GENERAL SYNTHETIC ROUTE TO EPOXYALKYLAMINES [J].
ASENSIO, G ;
MELLO, R ;
BOIXBERNARDINI, C ;
GONZALEZNUNEZ, ME ;
CASTELLANO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3692-3699
[4]   A general and efficient method for the monohydroxylation of alkanes [J].
Asensio, G ;
Mello, R ;
GonzalezNunez, ME ;
Castellano, G ;
Corral, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (02) :217-218
[5]   Oxyfunctionalization of aliphatic esters by methyl(trifluoromethyl)dioxirane [J].
Asensio, G ;
Castellano, G ;
Mello, R ;
Nunez, MEG .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5564-5566
[6]   Evidence for the involvement of a sulfurane intermediate in the oxidation of simple sulfides by methyl(trifluoromethyl)dioxirane. [J].
Asensio, G ;
Mello, R ;
GonzalezNunez, ME .
TETRAHEDRON LETTERS, 1996, 37 (13) :2299-2302
[7]   REGIOSELECTIVE OXYFUNCTIONALIZATION OF UNACTIVATED TERTIARY AND SECONDARY C-H BONDS OF ALKYLAMINES BY METHYL(TRIFLUOROMETHYL)DIOXIRANE IN ACID-MEDIUM [J].
ASENSIO, G ;
GONZALEZNUNEZ, ME ;
BERNARDINI, CB ;
MELLO, R ;
ADAM, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) :7250-7253
[8]   I(PY)2BF4, A NEW REAGENT IN ORGANIC-SYNTHESIS - GENERAL-METHOD FOR THE 1,2-IODOFUNCTIONALIZATION OF OLEFINS [J].
BARLUENGA, J ;
GONZALEZ, JM ;
CAMPOS, PJ ;
ASENSIO, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (04) :319-320
[9]   A GENERAL AND USEFUL COPPER(II)-PROMOTED IODOFUNCTIONALIZATION OF UNSATURATED SYSTEMS [J].
BARLUENGA, J ;
RODRIGUEZ, MA ;
CAMPOS, PJ ;
ASENSIO, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (19) :1491-1492
[10]   NOVEL OXIDATIVE ELIMINATION IN A NORBORNYL IODIDE [J].
BEELEY, NRA ;
SUTHERLAND, JK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (09) :321-322